Method for using levulinic acid to prepare gamma-valerolactone by hydrogenation

A technology of levulinic acid and levulinic acid solution, which is applied in chemical instruments and methods, metal/metal oxide/metal hydroxide catalysts, organic chemistry, etc., can solve the problem of difficulty in adapting to large-scale industrial production and product GVL yield Low cost and high cost of chemical reduction method, to achieve excellent hydrogenation activity and product selectivity, high product yield and low cost

Active Publication Date: 2012-08-01
CHINA UNIV OF PETROLEUM (EAST CHINA)
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  • Abstract
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Problems solved by technology

[0006] Due to the high cost of the chemical reduction method, it is difficult to adapt to large-scale industrial production. Most of the public patents of the catalytic hydrogenation method use noble metal catalysts such as Ru and Pt, which also have the problem of high catalyst cost and difficulty in industrial application.
The patented method of using non-precious metal catalysts such as nickel and copper has the problem of rapid decline in catalyst activity due to the acidity of the raw material LA itself. If Raney nickel is used, in order to maintain the catalyst activity, it is necessary to first convert LA into the corresponding sodium salt. , GVL can only be obtained through acidification after hydrogenation, the operation process is relatively cumbersome, and the yield of the product GVL is not high

Method used

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  • Method for using levulinic acid to prepare gamma-valerolactone by hydrogenation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1: 10 grams of copper-aluminum alloy powder containing 5.48% nickel, slowly add 65 milliliters of inorganic alkali solution containing 15 grams of NaOH at room temperature, heat up to 70°C for activation for 1 hour under stirring, and use 500 milliliters of 60°C deionized Wash with water until the pH is 8, and then replace the deionized water with absolute ethanol. Levulinic acid was slightly heated to be liquid, and 50 milliliters and 200 milliliters of methanol and the skeleton copper catalyst prepared above were added to the autoclave at the same time, and 0.6 grams of NaOH was added. The hydrogenation reaction temperature was controlled at 130-140° C., the hydrogen pressure was 3.0 MPa, and the reaction was continued for 2 hours. It was measured that the conversion rate of levulinic acid was 99.8%, and the selectivity of γ-valerolactone was 97.2%.

Embodiment 2

[0015] Example 2: 12 grams of copper-aluminum alloy powder containing 5.48% nickel, slowly add 70 milliliters of inorganic alkali solution containing 16 grams of NaOH at room temperature, heat up to 60 ° C for 1.5 hours under stirring, and use 500 milliliters, 50 ° C deionized Wash with water until the pH is 8, and then replace the deionized water with absolute ethanol. The levulinic acid was slightly heated to be in a liquid state, and 60 ml and 190 ml of dioxane and the skeleton copper catalyst prepared above were added to the autoclave at the same time, and 0.4 g of KOH was added. The hydrogenation reaction temperature is controlled at 130-140° C., the hydrogen pressure is 4.0 MPa, and the reaction is continued for 2.5 hours. The conversion rate of levulinic acid is 99.7%, and the selectivity of γ-valerolactone is 95.6%.

Embodiment 3

[0016] Embodiment 3: Change the copper-aluminum alloy powder activation condition in embodiment 1 into 70 ℃ of activation 1.5 hours, the levulinic acid hydrogenation reaction solvent is dehydrated alcohol, other catalyst activation methods and hydrogenation reaction conditions are the same as embodiment 1 The hydrogenation conversion rate of levulinic acid was 99.5%, and the selectivity of γ-valerolactone was 96.8%.

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Abstract

The invention discloses a method for using levulinic acid to prepare gamma-valerolactone by hydrogenation. Skeleton copper is used as a catalyst, copper-aluminum alloy as a catalyst precursor contains Group VIII transition metals to improve the activity and selectivity of the skeletal copper catalyst, the copper-aluminum alloy is extracted and activated by inorganic base solution to prepare the skeletal copper catalyst with the functions of hydrogenation and the functions of a molecule lactonization loop-locked, appropriate quantities of skeletal copper catalyst, additives and solvent added into the liquid-phase hydrogenation system of levulinic acid, and the catalyst can be continuously recycled. The method has the advantages of low catalyst cost, simple process, easiness in operation and high yield of gamma-valerolactone.

Description

Technical field: [0001] The invention relates to a method for preparing gamma-valerolactone from levulinic acid. Background technique: [0002] Levulinic acid (LA) is a product of acid hydrolysis of hexose and can be obtained from hydrolysis of cellulosic substances. Under the action of an appropriate catalyst, the catalytic hydrogenation of LA and its esters can produce high value-added products γ-valerolactone (GVL, also known as 5-valerolactone or 5-methylbutyrolactone). [0003] GVL can be used in food flavors or tobacco flavors, as well as solvents, fine chemical synthesis intermediates, etc. GVL can be prepared from LA by chemical reduction method and catalytic hydrogenation method. The chemical reduction method has a high cost and is only suitable for small-scale production. For example, Chinese patent CN101633649B discloses the use of KBH in NaOH solution for LA 4 Method for preparing GVL by chemical reduction. [0004] The preparation of GVL by catalytic hydrogen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33B01J23/755
CPCY02P20/584
Inventor 赵会吉刘晨光景美波殷长龙柴永明赵瑞玉张孔远柳云骐
Owner CHINA UNIV OF PETROLEUM (EAST CHINA)
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